A True Leader

I have always turned to books at times in my life when I was up against a new challenge. Books on teaching, coaching, negotiations, parenting, gardening, and instruction have served as joyful guides throughout my career and life.

That is why as I make my latest career change I am a bit perplexed as I wonder if books will still offer the key to success. Sure, I still love books— maybe somewhat obsessed— but I have begun to understand that the most valuable lessons can be found when we lift our eyes and look around us at the people we interact with each day.

This uncertainty began shortly after I was named as the successor to our iconic Superintendent effective August 2020.

I immediately started preparing by taking refuge in leadership books, starting with  Principles by Ray Dalio and The Ride of a Lifetime by Robert Iger. Both offered excellent insights in the quest to figure out what it takes to be the type of leader I want to be: someone who is fair, ethical, open, optimistic, innovative, and brave.

Yet, the more I read, the more I realized that the message Dalio and Iger were advocating for were on display for me in real life for the past 13 years. It is with that understanding and gratitude that my confidence rises knowing that  I have learned some much about what it takes to be a great leader about leadership from my Superintendent, Ileana Eckert.

I can’t help to think back to this past summer when her retirement was announced.

It is rare that secrets are kept in our  District and I suspect that is the norm in many places of work. Getting surprised is something that has not happened to me often in my educational career so when it happened, I was not prepared for the flood of emotions that I faced.

The day before I was dropping my oldest to the University of Buffalo for his freshman year, I was already fighting emotions and the pit that arrives in your stomach when you realize life as you know it is about to change.

Distracting myself with the work, I was feverishly getting ready for the upcoming school year. Managing to keep it all together and to my surprise my wife was as well. That was until my boss delivered the bombshell, that this would be her last year and she would be retiring at its conclusion.

I shut my laptop and snapped to attention as she explained to her Cabinet that although she loved the work, loved working with our teachers, administrators, Board of Education and central office team, that it was time to enjoy the next stage in her life. She wanted to be there for her granddaughters, she wanted to do volunteer work, she wanted to support her children, and, most of all, she wanted to enjoy a few years of retirement of her own before her husband decided to retire as well, a sort of stay-cation if you will.

There are very few people in this world that I respect as much as Ileana Eckert. Very few people who have taught me as much, very few people who have inspired me as much, and very few who have made me want to be a better person like she has. So hearing this news was not only shocking, it was emotional.

In typical “Ily” fashion she delivered an inspirational, heartfelt message about students at risk, the difference teachers can make and how much the teachers of North Rockland make her proud.  Then almost as an afterthought she put up a picture of her two granddaughters holding up a sign that stated Abuela is retiring July 2020.  She explained that she loved the work, loved the District, but wanted to take the opportunity to spend more time with her “little munchkins”

After a few gasps and a room full of tears, Mrs. Ileana Eckert received one of the longest, most sincere standing ovations I have ever had the pleasure of participating in. The emotions that crossed her face seemed to go from happiness, to nostalgia, to embarrassment. Our humble leader never did it for the accolades, or applause, or the power; she simply leads because she cares about our District, our community, and our children. She truly wants what is right, what is best; she has no hidden agenda, she lacks ego.

Her story serves as an inspiration to not only our staff, but also our significant number of English Language learners.  She came to The United States as a 5th grader who had been a successful student from a hardworking family of business owners. That was until one day, under the Castro regime, the Cuban government showed up at their store announcing the government was now in charge.

Her father, seeing the direction the country was heading, started the red tape-ladened process to come to America.  As Ily explains, after a year long process, a process in which every one of the family’s possessions needed to be accounted for and should anything break or go missing,  the journey could be jeopardized.

It is not often Ily tells stories of her past, but I have been lucky enough to hear her stories as a young girl in Cuba, a newcomer in a distant world, and how her father, a hardworking man of integrity, built a new life for his family, starting over well into his fifties.

I am sure he would be proud to see his daughter now as a respected leader in what was once a foreign land.

I love to listen, usually on car rides to sporting events or other school events as she describes her memories of growing up, the admiration she has for her family, and the lessons on life and leadership she skillfully embeds in her tale of the American dream. Her stories are a delight. Her story is an inspiration. To go back to the school she was once a language learner, to become its Superintendent, a position that is woefully underrepresented by women, is a story that should be shared.

There is so much I have learned from her, and so much more to learn, which makes her departure all that much more difficult  to accept.

Knowing that the chance of her moving out of North Rockland is less than the proverbial slim and none gives me comfort.  As does knowing how giving, caring, and selfless she is.

This helps to put my mind at ease because she is the type of person that is there for you before you know you need her.

One thing I have found common place in many of the leadership books I am perusing is some sort of manifesto, list of guiding principles, or ideals to follow.  Although Mrs. Eckert has never expressed what hers are, seeing her in action over the last 13 years, it has become pretty obvious in her consistent actions that she is guided by a set of convictions that she rarely strays from.

This is what I have learned from observing my boss.

Prioritize people

I have watched first hand as my boss has put people first and foremost in any decision she makes and in her daily interactions.  Being there for others in tough times may mean canceling a meeting or two to be at a funeral, a wake, to visit a sick child or visit an employee. It doesn’t matter how busy things get, making time for a card, a cake, a present, those are what our leaders’ priorities are. Things may be stressful, big decisions may need to be made, time may be short, yet no matter who she is with my boss makes them feel like they are the most important person in the world; she gives her full attention, makes eye contact, laughs, cries and listens to the person she is with. It doesn’t matter if they are a top politician, a 95 year old retiree, a custodian, or a kindergartener, Ileana makes you feel special. It should not come as a surprise that people not only respect her, but also feel comfortable speaking to her, certainly a trait we can all strive for!

Be humble

It is challenging to be a leader, to rise up the organizational hierarchy without congratulating yourself on occasion.  Leaders need to be confident, secure, true to their convictions. Yet I have learned from Mrs. Eckert that you can be confident and you can be strong, without a need for accolades, without the need for credit. She is a leader who cares little for what position you hold, what you look like, where you came from; she cares more about who you are and what you can do to make our schools and our community a stronger place.

Do not get in the mud

She is one of the few people I know who has absolutely no social media presence.  She sees that it can become a time suck, that can lead to gossip, rumors and innuendos.  Even though I am jokingly referred to as Dr. Twitter by some in my District and do see the value in social media in a lot of ways, she has a point. This is a leader that is above all of the pettiness of the social media world. She does not read it when the wannabe meteorologists criticize her latest call on school closing. She doesn’t feel the need to defend herself when a local reporter breaks apart her employment contract in a click bait effort. Even if it would be easy for her to point out that despite being one of the longest standing superintendents in our area, in one of the largest Districts, her compensation package is much less than her counterparts make. She does not feel it is necessary to point out that she has not collected the $10,000 health insurance buyout she was entitled to in her contract because “she didn’t feel it was the right thing to do” even if doing so meant $100,000 over the past 10 years of employment. This is a leader who stays above it all and is able to sleep well at night knowing that no matter what mud is slung, she has stayed true to her morals.

Laugh and love what you do

One of the best things about my job is that we can still laugh; we laugh at the absurd situations we deal with, we laugh at ourselves and each other.  Even when things become tense, we are encouraged to stop, laugh, love our students, enjoy a good meal, a good conversation, or a good lesson. I have learned from Ileana that no matter what you do, no matter where you are, there is enjoyment to be had.

Enjoy the moment

It is difficult to balance everything in work and in life.  As a school leader in North Rockland, our Superintendent feels it is essential to be there for our students, for our teachers, and for our staff.  This has meant long car rides to Syracuse to watch our bowling team compete in states. This has meant late nights watching concerts, plays, dances, and celebrations. This has meant spending weekends following various athletic teams around the county bundled up in her North Rockland Red Raider gear. How does she do it?  She truly loves every single moment of it; her smiles are not an act. She loves listening to the off pitch wails of a 6th graders turn into a Broadway like performance as students grow into their instruments and themselves by the time they graduate. When asked how come she gets so excited about bowling matches she looks confused and replies, “Because it is our kids and they are amazing.”  She loves every minute celebrating our District’s successes and is there for all of us as a shoulder to cry on when we fail. This type of love can not be faked and the kids know it. This was evident when the bowling team paid homage to her with a personalized bowling jersey and cake celebrating her retirement.

Be patient

I have learned from Ileana Eckert that sometimes it is better to just listen and learn.  The best leaders do not always act immediately; they think, they research, they give all parties a voice before making a decision.

Work hard

This goes without saying, you do not get where she is without a strong work ethic, but hers is somewhat legendary. One board member often asks only somewhat jokingly if she has a clone because she is everywhere all the time.

You can be strong and nice

Mrs. Eckert is one the nicest people I know.  She cares deeply about people, about what is right, and sincerely wants what is best for others. Her kindness should never be mistaken for weakness. She is unafraid to make difficult decisions, or to have difficult conversations. I have learned from her that you can disagree with someone, you can tell others no, you can fight for what is right, but you can do it in a respectful and kind way. This approach does not make you weaker in my opinion, it actually makes you a stronger leader and person.

Forgive and see the best in people

I often struggle with forgiveness.  I have a nagging sensation deep in my belly when I feel I have been wronged or those I care about have been wronged. I know this is a fault, I know I can and should do better.  Watching this leader forgive others, always see and expect the best in others, even when they have wronged her, is a trait I am trying to live up to. It is a trait I know will help me to be a better superintendent.  Watching my boss act with a heart of forgiveness for the past 13 years has been a huge help in reaching this goal.


Work is important and my boss has an important job, yet she always prioritizes her family and insists her employees do as well. That is why when a picture of her granddaughters flashed across the screen on opening day announcing Abuela’s retirement so she could babysit them, none of us could begrudge her.

Be Optimistic

The best leaders are optimistic, they see the bright side of the most difficult situations. It is with her optimism and positivity that allowed her to successfully guide our District through a 200 million dollar tax certiorari, the largest in state history.  We not only survived, but we have become stronger, more resilient, more creative. That is an accomplishment that could not have been achieved without the guidance of a leader who believed if we worked hard and worked together, we could accomplish anything.

It is difficult when a leader you respect and care about moves on. It is an even bigger challenge to replace a person who is an exemplary leader. Yet I have learned one more important lesson from my boss as I embark on this new journey. You can not be someone else, you have to be true to you and utilize your own style. Luckily for me, I have had the opportunity to work for great leaders like Ileana Eckert who have helped shape me and my beliefs. Will I be Ily?  Certainly not, but having had the opportunity to work alongside her worked has helped to prepare me for the challenge. My strong desire to not let her down will drive me to continue to improve, evolve, and grow into the leader our District deserves.